Premium
Cover Picture: Synthesis and Characterization of N,N′‐Substituted 15,15,16,16‐Tetracyano‐6,13‐pentacenequinodimethane‐2,3,9,10‐tetracarboxylic Diimide Derivatives (Asian J. Org. Chem. 3/2013)
Author(s) -
Wu Ti,
Chen Jianming,
Guo Yunlong,
Yu Gui,
Shuai Zhigang,
Liu Yunqi
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201390006
Subject(s) - diimide , chemistry , imide , homo/lumo , delocalized electron , molecule , crystallography , polymer chemistry , stereochemistry , organic chemistry , perylene
The design and synthesis of a series of N , N ′‐substituted 15,15,16,16‐tetracyano‐6,13‐pentacenequinodimethane‐2,3,9,10‐tetracarboxylic diimide (TCPQDI) derivatives that comprise a TCPQ core and two dicarboxylic imide groups is described by Yunqi Liu and co‐workers in their Communication on page 220 ff. The optimized geometry of TCPQDI is distorted from planarity and the molecule adopts a butterfly‐type structure. The tetracarboxylic diimide units increase α‐delocalization and lead to lower LUMO energy levels, which indicates that the incorporation of imide groups is a good strategy to decrease energy levels.